Sodium Carbonate → HCID 59699930, compound

HRID 1820067Notes

Reaction equation

HRID 1820067 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[CH2:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O)[CH3:23].C(=O)([O-])[O-].[Na+].[Na+].[N:39]1[CH:44]=[CH:43][CH:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:40]=1>O.CN(C=O)C.Cl[Pd-2](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[CH2:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:41]3[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=3)[CH:3]=2)[NH:8][CH:9]=1)[CH3:23]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59699930HCID 59699930, compoundYield 61.7%

Reagents, catalysts & solvents 4

HCID 178418903HCID 178418903, compoundCatalyst2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To 5-bromo-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (15 mg, 0.0314 mmol, prepared as described in method 1), 2-ethylphenyl boronic acid (5.2 mg, 0.034 mmol), and dichlorobis(triphenylphosphino)palladium (II) (1.3 mg, 0.0002 mmol) in a Smith process vial was added 0.5 mL of a 1:1 mixture of acetonitrile, and a 2 M solution of sodium carbonate in water. The reaction mixture was stirred for 6 h, then 3-pyridyl boronic acid pinacol ester (8.4 mg, 0.041 mmol) and dichlorobis(triphenylphosphino)palladium (II) (1.3 mg, 0.0002 mmol) were added and the reaction was run in a Personal Chemistry® microwave reactor at 150° C. for 900 s. The mixture was diluted with DMF (2 mL), filtered on a silica plug, and solvent was evaporated. Purification by reverse phase chromatography using a gradient of H2O and acetonitrile (with 0.1% formic acid as a modifier) afforded 3-(2-ethyl-phenyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine as a solid (5.8 mg, 61% yield). 1H NMR (1500 MHz, DMSO-d6) δ 1.05 (t, J=7.5 Hz, 3H), 2.66 (q, J=7.5 Hz, 2H), 7.27 (t, J=7.0 Hz, 1H), 7.31 (t, J=7.0 Hz, 1H), 7.38 (d, J=7.5 Hz, 2H), 7.45 (dd, J=5.5, 8.5 Hz, 1H), 7.60 (s, 1H), 7.98 (d, J=2.0 Hz, 1H), 8.10 (dd, J=1.5, 8.0 Hz, 1H), 8.54 (d, J=5.0 Hz, 1H), 8.60 (d, J=2.0 Hz, 1H), 8.90 (s, 1H), 12.0 (s, 1H). MS: m/z 300 (M+H+).

Workup

  1. waitthe reaction was run in a Personal Chemistry® microwave reactor at 150° C. for 900 s
  2. filtrationfiltered on a silica plug, and solvent
  3. customwas evaporated
  4. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-18a5b6a3055f45409e385ae420669084
Source dataset
uspto-grants-2009_10
Patent number
US07601839B2

Reaction notes

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